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Discarding the Negative

DAN SMITH  |  Oct 19, 2025

People think being an income tax preparer is all about possessing some super-human knowledge of the income tax code. It’s not. With the proper amount of continuing education and good computer software, you too could become a tax preparer. But to be a good one, you have to excel at customer service. You have to be accurate and thorough, you need to answer the phone and to be there for your customers. 
Still, sometimes, I had to let a client go.

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The Final Curtain Call: My Double Retirement

Mark Crothers  |  Oct 19, 2025

As a business owner, I was constantly required to be in the customer spotlight, which unfortunately meant adopting an extroverted façade—a sharp contrast to my naturally introverted self. My professional life, with its constant interaction and performative elements, was the biggest stage for this alter ego. Essentially, I was an entrepreneur with a separate, exhausting full-time job: character actor.
My favourite part of the day was 5 a.m., sitting in the sunroom with a coffee while my wife Suzie and the children were still asleep—the calm before donning my character mask and heading out for the day’s business.

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Have you ever met “they?” 

R Quinn  |  Oct 18, 2025

Have you ever met “they?”  Me neither, but from what I hear, he or she is a pretty bad dude.
“They” is responsible for every ill we face from rent prices to mortgage interest rates and student loans. “They” have caused housing prices to rise and inflation too.  “They” have rigged the system, even health insurance premiums. “They” made Social Security a scam. “They” is why people don’t earn what they think they should. 
“They” seem have total control over our economy with the ability to Ignore supply and demand and prices. 

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Housing options for older Americans

Nick Politakis  |  Oct 18, 2025

I wanted to share this article and I hope our dear HD readers comment and tell us if they are doing what is suggested in the article and how it’s working out.  I am at the beginning of trying to figure out my housing options and what is described in the article sounds good.
https://www.wsj.com/lifestyle/relationships/new-housing-options-emerge-for-older-americans-dfa4c8f5?st=Sp9vyR&reflink=desktopwebshare_permalink

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Money Pit

Catherine  |  Oct 18, 2025

It’s time to rewatch the 1986 Tom Hanks/Shelley Long cautionary tale about their dream house gone wrong.
After spending last year’s home improvement efforts on my newly-acquired tin can casita, my used car of a fishing cabin in the Sonoran Desert, I’m back in the city for some long-pondered home renovation. It ain’t been pretty, at least when I review the hit to my portfolio. Everything from a piece of lumber to a square foot of cement is more expensive than I’d imagined.

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It is never too late. By Chris

baldscreen  |  Oct 18, 2025

I would like to dedicate this post to Jonathan.
My spouse and I started with nothing. We left college with debt and moved to a HCOL area in the mid 1980s. We knew nothing about money other than “if you can’t pay your credit card off each month, quit charging until it is paid off”.
We are Christians and felt called to tithe our income, so we worked up to the full 10% of gross income that is traditional.

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Is The Stock Market Overvalued?

Adam M. Grossman  |  Oct 18, 2025

STOCK MARKET INVESTORS are enjoying yet another strong year. The S&P 500 has gained about 14% so far, shrugging off, for the most part, uncertainty over tariffs, interest rates and the latest government shutdown.
Should this worry us?
Since ancient times, soothsayers have been attempting—without luck—to forecast the future. As it relates to investment markets, the frustrating reality is that no one knows what the future will bring. But that doesn’t mean there’s nothing we can do.

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Backdoor Roth Explained

Bogdan Sheremeta  |  Oct 18, 2025

ROTH IRA IS A powerful account. It grows tax-free and withdrawals are tax-free during retirement. Roth IRA also has income limits.
For 2025, if you are filing your taxes as single and make less than $150,000 ($236,000 if married filing jointly) of modified adjusted gross income, you can contribute a maximum amount of $7,000.
But if you make $165,000 (single) or $246,000 (married jointly), you are ineligible to contribute to a Roth IRA directly.

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Easy DAF (e.g. Daffy.org) for Donation of Appreciated Stocks

Suzee  |  Oct 17, 2025

Hello, Humble Dollar community!!  This is my first post, please excuse me in advance if not as articulate as so many of you who contribute to this site.
I am wondering if any of you have recommendations or thoughts on simple DAF platforms for charitable contributions
I have some highly appreciated stock (APPL at ~$250/share with a very low basis) and use this for most of my larger charitable gifts.  I am a devoted Vanguard customer and make direct donations thru Vanguard but tend to find the process a bit tedious –

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Calling All HD Writers

Bogdan Sheremeta  |  Oct 17, 2025

I wanted to follow up on R Quinn’s forum post about HD writers and encourage everyone to submit your own articles for posting.
Many people mentioned that they’re unsure what to write about, so here are a few ideas to get you started:
> What I wish I knew about money before turning X
> How my relationship with money changed after X happened
> The emotional side of retiring, and learning to spend the money I saved
>

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ACA Subsidies for Early Retirees

kristinehayes2014  |  Oct 17, 2025

One of the greatest benefits I received  from my last employer was the gift of health care insurance in my retirement years. At the time I was hired (almost 28 years ago), they offered an early retiree benefit: work for twenty years and, if you chose to retire after you turn 55, you could continue to receive coverage as if you were an active employee. Needless to say, it’s a benefit they no longer offer.
I retired on my 55th birthday,

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Digital Lockout: A Cautionary Tale 

Mark Crothers  |  Oct 17, 2025

I recently flew to Spain to meet a friend who was coming from London. We enjoyed a few lovely days together until disaster struck. After spending an hour at the pool, my friend went to check his phone for the time—only to realize he’d forgotten to take his phone out of his swimming shorts pocket. By then, it was too late: the phone had slipped out and been sitting at the bottom of the pool the entire time.

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Drinking on the Job

DAN SMITH  |  Oct 16, 2025

I’m blaming Nick for this post, which has nothing to do with retirement. Still, I thought you may enjoy hearing about the drinking culture in the beer business, in the 70s.
My first job in the beverage business was as a driver-salesman for Pepsi. After several years I decided to pursue a job selling beer. It was 1977, I was 24 when I applied for a job and was called for an interview at the beer distributor.

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351 Exchange – Tax-Free Transfer of Individual Stocks to an ETF

Ed Kadala  |  Oct 16, 2025

In an effort to simplify and consolidate my portfolio, I recently completed what’s known as a Section 351 exchange in a taxable account. This provision of the Internal Revenue Code lets investors transfer assets—such as stocks and securities—to a corporation without recognizing a taxable gain or loss, provided certain conditions are met.
With help from my financial consultant, I exchanged a portfolio of individual stocks in a separately managed account (SMA), held since 2020, for shares in a new exchange-traded fund (ETF).

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Healthcare Insurance Alternatives to Covered California Marketplace

Bradley Brechin  |  Oct 16, 2025

We are a couple who retired early (early 60s) and like many are facing a big jump in our Healthcare costs (California residents). Has anyone here looked at alternatives to the marketplace, such as insurance brokers, for Healthcare? Any recommendation or insight would be welcome. Also, I searched the articles and couldn’t find anything about this. Thank you.

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